It was originally listed for sale with a $5.75 million price tag in November 2015, before being reduced to $5.15 million and removed from the market in December.

It was last sold for $3.275 million in 2008 to Marlene Iglitzen, the widow of the late Chicago film critic and “At The Movies” host Gene Siskel, according to listing records and reports from the Chicago Tribune.

The apartment is on the third floor of the mansion, which is located on North State Parkway and was built in 1899 for a wealthy Chicago doctor, according to Curbed.

But that’s not what it’s most famous for. That happened in the 1959, when Chicago native Hugh Hefner moved in and started his empire, before he headed west in the 1970s and moved into his Holmby Hills, Los Angeles, Playboy mansion, which he still lives in, although it was recently sold.

According to the Chicago Tribune, Mr. Heffner’s office was located in his bedroom, and house guests included all five Rolling Stones members and Warren Beatty.

He lived on the second floor; the third and fourth floors, meanwhile, eventually became Bunny dorms where rent was $50 a month.

Features of the condo for sale include a dining room, eat-in kitchen, home office, en-suites in all bedrooms, a covered terrace and parking space for two cars.

“I bought it five days after it was listed,” Ms. Iglitzen said in a statement to the Tribune when the condo first hit the market.

“It was everything I wanted in a home: enormous windows in all directions, large scaled rooms and an outside deck outside the kitchen for gardening and grilling. I can see the trees turning each season. It’s a private home within a mansion.”